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ChemicalBook CAS DataBase List 3-Quinolineboronic acid
191162-39-7

3-Quinolineboronic acid synthesis

5synthesis methods
-

Yield:191162-39-7 90%

Reaction Conditions:

with n-butyllithium;Triisopropyl borate in tetrahydrofuran;hexane at -78; for 1 h;Inert atmosphere;Schlenk technique;

Steps:

2.2.5 2-Naphthalenyl boronic acid (2NB)
General procedure: To a two-neck 250mL round bottom flask, triisopropyl borate (3.30mL, 29.06mmol) and 3-bromoquinoline (3.00g, 14.49mmol) was dissolved in dry THF (100mL), then n-butyllithium (14.50mL of a 2M solution in hexane, 29.00mmol) was added dropwise via a dropping funnel over 1h under N2 at-78°C. After 2h, the acetone/dry ice bath was removed, and the reaction solution was allowed to warm to 0°C. The reaction was then quenched with a 2M HCl solution, and the pH value was adjusted to 7 with a solution of 2M NaHCO3. The resulting solution was extracted with ethyl acetate (EA) (3×100mL). The combined organic layers were dried with MgSO4 and evaporated to dryness. n-Hexane was then added to precipitated the product as a white solid (80% yield).

References:

Wang, Jianli;Leung, Louis M. [Dyes and Pigments,2013,vol. 99,# 1,p. 105 - 115]

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